WO1997024230A1 - Plasticized polyvinyl butyral and sheet - Google Patents
Plasticized polyvinyl butyral and sheet Download PDFInfo
- Publication number
- WO1997024230A1 WO1997024230A1 PCT/US1996/020099 US9620099W WO9724230A1 WO 1997024230 A1 WO1997024230 A1 WO 1997024230A1 US 9620099 W US9620099 W US 9620099W WO 9724230 A1 WO9724230 A1 WO 9724230A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sheet
- pvb
- plasticized
- plasticizer
- polyvinyl butyral
- Prior art date
Links
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 title claims abstract description 38
- 229920005989 resin Polymers 0.000 claims abstract description 20
- 239000011347 resin Substances 0.000 claims abstract description 20
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 16
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- FRQDZJMEHSJOPU-UHFFFAOYSA-N Triethylene glycol bis(2-ethylhexanoate) Chemical compound CCCCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CCCC FRQDZJMEHSJOPU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004014 plasticizer Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000002269 spontaneous effect Effects 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- -1 butyraldehyde acetal Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000156 glass melt Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 238000001374 small-angle light scattering Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10605—Type of plasticiser
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2329/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
- C08J2329/14—Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31627—Next to aldehyde or ketone condensation product
- Y10T428/3163—Next to acetal of polymerized unsaturated alcohol [e.g., formal butyral, etc.]
Definitions
- This invention relates to plasticized polyvinyl butyral (PVB) and more particularly PVB sheet containing compatible plasticizer.
- Plasticized PVB sheet is used in light- transmitting laminates containing one or more rigid layers, such as glass, for applications such as building and vehicle windows, show cases, protective glass for pictures, documents and the like.
- the plasticized sheet absorbs energy and prevents disintegration when, for example, the head of a vehicle occupant strikes the rigid layer of a laminate window after a sudden stop or a foreign object is propelled against the outside of the laminate.
- the PVB resin contains hydroxyl groups in the polymer chain to promote adhesion to glass.
- the plasticizer must be carefully chosen to contribute to a balance of performance properties in the laminate. Cost/benefit performance continues of importance in assessing plasticized PVB for safety laminates having valuable commercial properties.
- plasticized PVB formulations have been developed exhibiting improved plasticizer and PVB compatibility (affinity of resin and plasticizer for each other) in comparison with prior art systems . Accordingly, a principal object of this invention is to provide plasticized PVB formulations exhibiting improved compatibility of plasticizer with PVB resin.
- Another object is to provide a compatible plasticized PVB formulation wherein the plasticizer is synthesized from readily available, relatively inexpensive starting materials.
- polyvinyl butyral resin having a hydroxyl content of less than 19.5, preferably about 17 to 19 weight % calculated as polyvinyl alcohol plasticized with a compatible amount of triethylene glycol di-2- ethylhexanoate (3GEH) .
- Triethyleneglycol di-2-ethylhexanoate in the PVB formulation plasticizes the PVB resin.
- the resin-compatible effective amount depends on properties desired in the laminate application. Generally 35 to 45 parts plasticizer per 100 parts PVB resin (PPHR) are used.
- PVB resin has a weight average molecular weight greater than 70,000, preferably about 100,000 to 250,000, as measured by size exclusion chromatography using low angle laser light scattering.
- PVB typically comprises less than 19.5%, preferably about 17 to 19% hydroxyl groups calculated as polyvinyl alcohol (PVOH) ,- 0 to 10%, preferably 0 to 3% residual ester groups, calculated as polyvinyl ester, e.g. acetate, with the balance being acetal, preferably butyraldehyde acetal, but optionally including a minor amount of acetal groups other than butyral, for example 2-ethyl hexanal as disclosed in U.S. 5,137,954, issued August 11, 1992.
- PVOH polyvinyl alcohol
- PVB resin is produced by known aqueous or solvent acetalization processes reacting PVOH with butyraldehyde in the presence of acid catalyst, followed by neutralization of the catalyst, separation, stabilization and drying of the resin. It is commercially available from Monsanto Company as Butvar ® resin.
- Plasticized PVB as sheet at a non- critical thickness of about 0.13 to 1.3 mm is formed by mixing resin and plasticizer and preferably (in commercial systems) extruding the mixed formulation through a sheet die, i.e.
- Sheet of the invention optionally contain additives to enhance performance such as dyes, pigments, ultraviolet light stabilizers, antioxidants, adhesion control salts and the like.
- additives to enhance performance such as dyes, pigments, ultraviolet light stabilizers, antioxidants, adhesion control salts and the like.
- Amounts and percentages are in weight .
- PVB Residual Hydroxyl (% PVOH) : ASTM 1396.
- Spontaneous Exudation - Measures plasticizer - PVB resin compatibility at the extremes of expected operating temperatures and humidity.
- Blend plasticizer and PVB formulated (in terms of plasticizer amount) to a glass transition temperature Tg of 31 +/- 1°C for 8 minutes at 150°C in a Brabender mixer equipped with sigma blades turning at 50 rpm.
- a heated hydraulic press 149°C, 5.5 MPa for 5 min.
- Place samples in a wet desiccator (enclosed chamber containing water to create 100% RH) held at various temperatures for 7 days. Lightly wipe exuded plasticizer from sample surfaces to remove exuded plasticizer and then dry the samples in a desiccator for 5 days. Calculate weight loss as % of initial plasticizer weight as spontaneous exudation.
- Sheet of various 3GEH plasticized PVB formulations was stored in roll form at 50°F (10°C) for about 9 months in a warehouse at sheet moisture content of about 0.4 to 0.6%.
- the sheet formulations were:
- Example 8 9 had an unacceptable surface film of plasticizer as compared with that of Examples 6, 7 which had none. This confirms in commercial use the lab results of Examples 1-5.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Joining Of Glass To Other Materials (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19960944432 EP0877665B1 (en) | 1995-12-29 | 1996-12-24 | Plasticized polyvinyl butyral and sheet |
| CA 2241653 CA2241653C (en) | 1995-12-29 | 1996-12-24 | Plasticized polyvinyl butyral and sheet |
| JP52437497A JP3675841B2 (ja) | 1995-12-29 | 1996-12-24 | 可塑化ポリビニルブチラール及びシート |
| AT96944432T ATE195686T1 (de) | 1995-12-29 | 1996-12-24 | Weichgemachtes polyvinylbutyral und damit hergestellte folie |
| DE69609992T DE69609992T2 (de) | 1995-12-29 | 1996-12-24 | Weichgemachtes polyvinylbutyral und damit hergestellte folie |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/580,952 US6559212B1 (en) | 1995-12-29 | 1995-12-29 | Plasticized polyvinyl butyral and sheet |
| US08/580,952 | 1995-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997024230A1 true WO1997024230A1 (en) | 1997-07-10 |
Family
ID=24323287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/020099 WO1997024230A1 (en) | 1995-12-29 | 1996-12-24 | Plasticized polyvinyl butyral and sheet |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6559212B1 (cs) |
| EP (1) | EP0877665B1 (cs) |
| JP (1) | JP3675841B2 (cs) |
| KR (1) | KR100452588B1 (cs) |
| CN (1) | CN1106278C (cs) |
| AT (1) | ATE195686T1 (cs) |
| CA (1) | CA2241653C (cs) |
| CZ (1) | CZ299865B6 (cs) |
| DE (1) | DE69609992T2 (cs) |
| ES (1) | ES2151193T3 (cs) |
| MX (1) | MX9805320A (cs) |
| PT (1) | PT877665E (cs) |
| WO (1) | WO1997024230A1 (cs) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10129422A1 (de) * | 2001-06-19 | 2003-01-02 | Huels Troisdorf | Weichmacherhaltige PVB-Folie |
| WO2004111115A1 (en) | 2003-06-09 | 2004-12-23 | Solutia Incorporated | Polyvinyl butyral sheet with bifunctional surface modifying agent |
| US6984679B2 (en) | 2001-01-09 | 2006-01-10 | Kurray Specialties Europe Gmbh | Plasticizer-containing polyvinylbutyrals, method for producing the same and the use thereof, especially for producing films for use in laminated safety glasses |
| WO2009135928A1 (de) * | 2008-05-08 | 2009-11-12 | Kuraray Europe Gmbh | Weichmacherhaltige folien aus polyvinylacetal mit cyclohexan-1,2-dicarbon-säureestern als weichmacher |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4216969B2 (ja) * | 1999-09-30 | 2009-01-28 | 積水化学工業株式会社 | 合わせガラス用中間膜及び合わせガラス |
| US6992130B2 (en) | 2002-07-23 | 2006-01-31 | Kuraray Co., Ltd. | Polyvinyl acetal and its use |
| MXPA05004456A (es) * | 2002-10-29 | 2005-07-26 | Du Pont | Intercapas de polivinilbutiral que tienen propiedades acusticas mejoradas y metodo de preparacion de las mismas. |
| US20050238887A1 (en) * | 2004-04-27 | 2005-10-27 | D Errico John J | Infrared reflecting multiple layer glass panels |
| DE102004043907A1 (de) * | 2004-09-10 | 2006-03-16 | Kuraray Specialities Europe Gmbh | Weichmacherhaltige PVB-Folien mit Etherbindungen enthaltenden Carbonsäureestern als Co-Weichmacher |
| US20060231189A1 (en) * | 2005-04-15 | 2006-10-19 | Solutia, Inc. | Low moisture polymer sheets |
| US20080064800A1 (en) * | 2006-09-08 | 2008-03-13 | Bruce Edward Wade | Poly(vinyl butyral) Dispersions Comprising a Non-Ionic Surfactant |
| KR20090073178A (ko) * | 2006-10-23 | 2009-07-02 | 덴끼 가가꾸 고교 가부시키가이샤 | 폴리비닐아세탈 시트 및 그 제조 방법 |
| US20080268204A1 (en) * | 2007-04-29 | 2008-10-30 | David Paul Bourcier | Multiple layer polymer interlayers having an embossed surface |
| US7901780B2 (en) * | 2008-06-25 | 2011-03-08 | Solutia Inc. | Polymer interlayers comprising blends of plasticized poly(vinyl butyral) and poly(cyclohexanedimethylene terephthalate-co-ethylene terephthalate) copolyester |
| EP2258546B1 (de) | 2009-05-12 | 2012-03-21 | Kuraray Europe GmbH | Verfahren zur Herstellung von laminierten Schichtkörpern mit dekorativen Gaseinschlüssen |
| DE102009027657A1 (de) | 2009-07-13 | 2011-01-20 | Kuraray Europe Gmbh | Weichmacherhaltige Folien aus Polyvinylacetal mit Adipatdialkylestern als Weichmacher |
| EP2548729A1 (de) | 2011-07-22 | 2013-01-23 | Kuraray Europe GmbH | Folien aus weichmacherhaltigem Polyvinyl(iso)acetal |
| US10005899B2 (en) * | 2014-12-08 | 2018-06-26 | Solutia Inc. | Blends of poly(vinyl acetal) resins for compositions, layers, and interlayers having enhanced optical properties |
| WO2016159208A1 (ja) * | 2015-03-31 | 2016-10-06 | 積水化学工業株式会社 | 合わせガラス用中間膜及び合わせガラス |
| US10668691B2 (en) | 2016-06-21 | 2020-06-02 | Solutia Inc. | Polymeric interlayers and multiple layer panels made therefrom exhibiting enhanced properties and performance |
| US10737470B2 (en) | 2016-06-21 | 2020-08-11 | Solutia Inc. | Polymeric interlayers and multiple layer panels made therefrom exhibiting enhanced properties and performance |
| US10589495B2 (en) | 2016-06-21 | 2020-03-17 | Solutia Inc. | Polymeric interlayers and multiple layer panels made therefrom exhibiting enhanced properties and performance |
| US10926516B2 (en) | 2016-06-21 | 2021-02-23 | Solutia Inc. | Polymeric interlayers and multiple layer panels made therefrom exhibiting enhanced properties and performance |
| US10611906B2 (en) | 2016-06-21 | 2020-04-07 | Solutia Inc. | Polymeric interlayers and multiple layer panels made therefrom exhibiting enhanced properties and performance |
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| JPH01252556A (ja) * | 1988-03-31 | 1989-10-09 | Kuraray Co Ltd | 安全合せガラス用中間膜組成物 |
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| US4276351A (en) | 1980-06-30 | 1981-06-30 | E. I. Du Pont De Nemours And Company | Polyvinyl butyral plasticized with tetraethyleneglycol di-2-ethylhexanoate |
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| JPS5846266A (ja) | 1981-09-12 | 1983-03-17 | Asahi Seikou Kk | 軸受箱の防塵装置 |
| DE3417653A1 (de) | 1984-05-12 | 1985-11-14 | Hoechst Ag, 6230 Frankfurt | Weichmacherhaltige thermoplastische polyvinylbutyralformmassen mit reduziertem haftvermoegen an glas |
| DE3417654A1 (de) | 1984-05-12 | 1985-11-14 | Hoechst Ag, 6230 Frankfurt | Reduzierung des haftvermoegens an glas von thermoplastischen, weichmacherhaltigen polyvinylbutyralformmassen |
| DE3429440A1 (de) | 1984-08-10 | 1986-02-20 | Hoechst Ag, 6230 Frankfurt | Polyvinylbutyral mit reduzierter klebrigkeit und verbesserter reissfestigkeit |
| JPS6146425A (ja) | 1984-08-11 | 1986-03-06 | Nippon Denso Co Ltd | デイ−ゼル機関用燃料噴射率制御装置 |
| GB8725744D0 (en) | 1987-11-03 | 1987-12-09 | Du Pont Canada | Dual-ovenable nylon container |
| US4942102A (en) * | 1988-01-15 | 1990-07-17 | E. I. Du Pont De Nemours And Company | Holographic optical elements having a reflection hologram formed in a photopolymer |
| JPH03154639A (ja) | 1989-11-13 | 1991-07-02 | Nippon Soken Inc | 金属製触媒担体 |
| JP3201778B2 (ja) * | 1991-06-26 | 2001-08-27 | 積水化学工業株式会社 | 合わせガラス用中間膜及びそれを用いた合わせガラス |
| DE4309638A1 (de) | 1993-03-25 | 1994-09-29 | Hoechst Ag | Weichmacherhaltige Polyvinylbutyrale mit gegenüber Silikatglas verbesserten haftungsreduzierenden Eigenschaften, Verfahren zu ihrer Herstellung und ihre Verwendung |
| JPH07172878A (ja) | 1993-12-22 | 1995-07-11 | Sekisui Chem Co Ltd | 合わせガラス用中間膜 |
| JP3154639B2 (ja) | 1994-04-21 | 2001-04-09 | 帝人株式会社 | 耐加水分解性芳香族ポリエステルおよび繊維 |
| KR100334149B1 (ko) | 1997-07-17 | 2002-04-26 | 니시자와 스스므 | 적층유리용 중간막 및 적층유리 |
-
1995
- 1995-12-29 US US08/580,952 patent/US6559212B1/en not_active Expired - Lifetime
-
1996
- 1996-12-24 KR KR10-1998-0704972A patent/KR100452588B1/ko not_active Expired - Lifetime
- 1996-12-24 CZ CZ0200298A patent/CZ299865B6/cs not_active IP Right Cessation
- 1996-12-24 WO PCT/US1996/020099 patent/WO1997024230A1/en active IP Right Grant
- 1996-12-24 AT AT96944432T patent/ATE195686T1/de active
- 1996-12-24 EP EP19960944432 patent/EP0877665B1/en not_active Expired - Lifetime
- 1996-12-24 ES ES96944432T patent/ES2151193T3/es not_active Expired - Lifetime
- 1996-12-24 DE DE69609992T patent/DE69609992T2/de not_active Expired - Lifetime
- 1996-12-24 PT PT96944432T patent/PT877665E/pt unknown
- 1996-12-24 CN CN96180142A patent/CN1106278C/zh not_active Expired - Lifetime
- 1996-12-24 CA CA 2241653 patent/CA2241653C/en not_active Expired - Lifetime
- 1996-12-24 JP JP52437497A patent/JP3675841B2/ja not_active Expired - Fee Related
-
1998
- 1998-06-29 MX MX9805320A patent/MX9805320A/es unknown
-
2003
- 2003-01-22 US US10/347,792 patent/US20030144396A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2274672A (en) * | 1938-04-30 | 1942-03-03 | Pittsburgh Plate Glass Co | Safety glass |
| JPH01252556A (ja) * | 1988-03-31 | 1989-10-09 | Kuraray Co Ltd | 安全合せガラス用中間膜組成物 |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6984679B2 (en) | 2001-01-09 | 2006-01-10 | Kurray Specialties Europe Gmbh | Plasticizer-containing polyvinylbutyrals, method for producing the same and the use thereof, especially for producing films for use in laminated safety glasses |
| KR100809198B1 (ko) * | 2001-01-09 | 2008-02-29 | 쿠라라이 유럽 게엠베하 | 가소화된 폴리비닐 부티랄, 그의 제조방법 및 적층 안전유리에 사용될 필름 제조를 위한 그의 용도 |
| DE10129422A1 (de) * | 2001-06-19 | 2003-01-02 | Huels Troisdorf | Weichmacherhaltige PVB-Folie |
| WO2004111115A1 (en) | 2003-06-09 | 2004-12-23 | Solutia Incorporated | Polyvinyl butyral sheet with bifunctional surface modifying agent |
| US7041375B2 (en) | 2003-06-09 | 2006-05-09 | Solutia Incorporated | Polyvinyl butyral sheet with bifunctional surface modifying agent |
| WO2009135928A1 (de) * | 2008-05-08 | 2009-11-12 | Kuraray Europe Gmbh | Weichmacherhaltige folien aus polyvinylacetal mit cyclohexan-1,2-dicarbon-säureestern als weichmacher |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2241653A1 (en) | 1997-07-10 |
| DE69609992T2 (de) | 2001-05-10 |
| PT877665E (pt) | 2000-12-29 |
| US6559212B1 (en) | 2003-05-06 |
| EP0877665B1 (en) | 2000-08-23 |
| ATE195686T1 (de) | 2000-09-15 |
| US20030144396A1 (en) | 2003-07-31 |
| JP2001515527A (ja) | 2001-09-18 |
| CZ200298A3 (cs) | 1999-05-12 |
| CA2241653C (en) | 2005-08-23 |
| CN1209092A (zh) | 1999-02-24 |
| MX9805320A (es) | 1998-10-31 |
| DE69609992D1 (de) | 2000-09-28 |
| ES2151193T3 (es) | 2000-12-16 |
| KR19990076845A (ko) | 1999-10-25 |
| EP0877665A1 (en) | 1998-11-18 |
| KR100452588B1 (ko) | 2004-12-23 |
| CZ299865B6 (cs) | 2008-12-17 |
| CN1106278C (zh) | 2003-04-23 |
| JP3675841B2 (ja) | 2005-07-27 |
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